1,1'-Carbonyldiimidazole → 2-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-pentanoic acid methyl ester

HRID 388452Notes

Reaction equation

HRID 388452 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])[CH2:5][CH2:6][CH3:7].[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:18])[CH:4]([N:8]1[C:9](=[O:17])[C:10]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:16][C:19]1=[O:20])[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 687288232-(2-Amino-benzoylamino)-pentanoic acid methyl ester

Product 1

HCID 687263392-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-pentanoic acid methyl esterYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-amino-benzoylamino)-pentanoic acid methyl ester (575 mg, 2.30 mmol) and 1,1′-carbonyldiimidazole (930 mg, 5.74 mmol) in THF (25 mL) is added 1,8-diazabicyclo[5.4.0]undec-7-enc (0.9 mL, 6.02 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with EtOAc (100 mL) and is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, concentrated and the resulting residue is purified by flash chromatography with 50% EtOAc in Hexane as the eluent to afford the desired 2-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-pentanoic acid methyl ester (284 mg, 45%).

Workup

  1. washis washed with H2O (50 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue is purified by flash chromatography with 50% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-abac5d5fc9b8450aa4c897bb745c438a
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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